Liquid triarylamines: The scope and limitations of piers-rubinsztajn conditions for obtaining triarylamine-siloxane hybrid materials

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 1663-1674

  Kamino, Brett A ^a   Mills, Bridget ^a   Reali, Christopher ^a   Gretton, Michael J ^a   Brook, Michael A ^b   Bender, Timothy P ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER COMPLEX; LEWIS ACIDIC; MOLECULAR LIQUIDS; OXIDATION POTENTIALS; REVERSIBLE REDOX REACTIONS; SUBSTITUTION PATTERNS; TRIARYLAMINES; TRIS(PENTAFLUOROPHENYL) BORANE; UV-VIS-NIR;

CATALYSTS; CHARGE TRANSFER; HYBRID MATERIALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PIERS; REACTION KINETICS; REDOX REACTIONS;

LIQUIDS;

AROMATIC AMINE; BORANE DERIVATIVE; SILOXANE;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; ELECTROCHEMISTRY; FLUORINE NUCLEAR MAGNETIC RESONANCE; NEAR INFRARED REFLECTANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

EID: 84857196343     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2020906     Document Type: Article

References (57)

1. Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Chem. Rev. 2009, 109, 897-1091
2. Brabec, C.; Scherf, U.; Dyakonov, V. Organic Photovoltaics: Materials, Device Physics, and Manufacturing Technologies; Wiley-VCH: Weinheim, Germany, 2008.
3. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Angew. Chem., Int. Ed. 2008, 47, 4070-4098
4. Borsenberger, P. M.; Weiss, D. S. Organic Photoreceptors for Xerography; Marcel Dekker Inc.: New York, 1998.
5. Shirota, Y.; Kageyama, H. Chem. Rev. 2007, 107, 953-1010
6. Snaith, H. J.; Zakeeruddin, S. M.; Wang, Q.; Péechy, P.; Grätzel, M. Nano Lett. 2006, 6, 2000
7. Hirata, S.; Kubota, K.; Jung, H. H.; Hirata, O.; Goushi, K.; Yahiro, M.; Adachi, C. Adv. Mater. 2011, 23 (7) 889-893
8. Xu, D.; Adachi, C. Appl. Phys. Lett. 2009, 95, 053304
9. Hendricks, E.; Guenther, B. D.; Zhang, Y.; Wang, J. F.; Staub, K.; Zhang, Q.; Marder, S. R.; Kippelen, B. L.; Peyghambarian, N. Chem. Phys. 1999, 245, 407
10. Ribierre, J.; Aoyama, T.; Kobayashi, T.; Sassa, T.; Muto, T.; Wada, T. J. Appl. Phys. 2007, 102, 033106
11. Ribierre, J. C.; Aoyama, T.; Muto, T.; Imase, Y.; Wada, T. Org. Electron. 2008, 9, 396
12. Kamino, B. K.; Castrucci, J.; Bender, T. P. Silicon 2011, 3 (3) 125-137
13. Kamino, B. K.; Grande, J. B.; Brook, M. A.; Bender, T. P. Org. Lett. 2011, 13, 154-157
14. Piers, W. E. In Adv. Organomet. Chem.; West, R.; Hill, A. F., Eds.; Elsevier Academic Press: San Diego, 2005; Vol. 52, p 1.
15. Brook, M. A.; Grande, J. B.; Ganachaud, F. Adv. Polym. Sci. 2010, 235, 161-183
16. Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440-9441
17. Rubinsztajn, S.; Cella, J. A. Macromolecules 2005, 38 (4) 1061-1063
18. Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887-4892
19. Zhou, D.; Kawakami, Y. Macromolecules 2005, 16, 6902-6908
20. Thompson, D. B.; Brook, M. A. J. Am. Chem. Soc. 2008, 1, 32-33
21. Chojnowski, J.; Fortuniak, W.; Kurjata, J.; Rubinsztajn, S.; Cella, J. A. Macromolecules 2006, 11, 3802-3807
22. Chojnowski, J.; Rubinsztajn, S.; Fortuniak, W.; Kujata J. Inorg. Organomet. Polym. Mater. 2007, 17, 173-187
23. Cella, J.; Rubinsztajn, S. Macromolecules 2008, 41, 6965-6971
24. Grande, J. B.; Gonzaga, F.; Brook, M. A. Dalton Trans. 2010, 39, 9369-9378
25. Grande, J. B.; Thompson, D. B.; Gonzaga, F.; Brook, M. A. Chem. Commun. 2010, 27, 4988-4990
26. Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090-3098
27. Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. E. Org. Lett. 2000, 2, 3921-3923
28. Thelakkat, M. Macromol. Mater. Eng. 2002, 287, 442-461
29. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar Roman, L. M. J. Org. Chem. 1999, 64, 5575
30. Jiang, L.; Stephan, B. L. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 13.
31. Bender, T. P.; Coggan, J. A.; McGuire, G.; Murphy, L. D.; Toth, A. E. J. US Patent 7,408,085, 2008.
32. Bender, T. P.; Coggan, J. A. US Patent 7,402,700, 2008.
33. Bender, T. P.; Goodbrand, H. B.; Hu, N. X.; US Patent 7,402,699, 2008.
34. Bender, T. P.; Coggan, J. A.; US Patent 7,345,203, 2008.
35. Coggan, J. A.; Bender, T. P. US Patent 7,332,630, 2008.
36. Lambert, C.; Nöll, G. J. Am. Chem. Soc. 1999, 121, 8434-8442
37. Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273
38. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723
39. Combes, S.; Finet, J. P. Tetrahedron 1998, 54, 4313-4318
40. Ku, C.; Kuo, C.; Chen, C.; Leung, M.; Hsieh, L. J. Mater. Chem. 2008, 18, 1296-1301
41. Janiak, C.; Braun, L.; Scharmann, T. G.; Girgsdies, F. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1998, C54 (11) 1722-1724
42. Di Saverio, A.; Focante, F.; Isabella, C.; Resconi, L.; Beringhelli, T.; D'Alfonso, G.; Donghi, D.; Maggioni, D.; Mercandelli, P.; Sironi, A. Inorg. Chem. 2005, 44 (14) 5030-5041
43. Szeghalmi, A. V.; Erdmann, M.; Engel, V.; Schmitt, M.; Amthor, S.; Kriegisch, V.; Nöll, G.; Stahl, R.; Lambert, C.; Leusser, D.; Stalke, D.; Zabel, M.; Popp, J. J. Am. Chem. Soc. 2004, 126, 7834-7845
44. Noviandri, I; Brown, K. N.; Fleming, D. S.; Fulvas, P. T.; Lay, P. A.; Masters, A. F.; Phillips, L. J. Phys. Chem. B 1999, 103, 6713
45. Saragi, T. P. I.; Spehr, T.; Siebert, A.; Fuhrmann-Lieker, T.; Salbeck, J. Chem. Rev. 2007, 107 (4) 1011-1065
46. Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61 (20) 6906-6921
47. Brunner, K.; Dujken, A.; Börner, H.; Bastiaansen, J. J. A. M.; Kiggen, N. M. M.; Langeveld, B. M. W. J. Am. Chem. Soc. 2004, 126 (19) 6035-6042
48. Carbazoles 13a - b as well as precursors 12a - b have been previously described. See: Takaki, K. S.; Bruce, M. A.; Poindexter, G. S.; Watson, B. T.; Yevich, J. P. US Patent 5,677,328, October 14, 1997.
49. Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164-5173
50. Nozaki, K.; Takahashi, K.; Nakano, K.; Hiyama, T.; Tang, H.; Fujiki, M.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2051-2053
51. Suzuki, K.; Hori, Y.; Kobayashi, T. Adv. Synth. Catal. 2008, 350, 652-656
52. Piers, W. E. In Adv. Organomet. Chem.; West, R.; Hill, A. F., Eds.; Elsevier Inc.: Amsterdam, 2005; Vol. 52, pp 1-76.
53. Kwaan, R. J.; Harlan, C. J.; Norton, J. R. Organometallics 2001, 20, 3818-3820
54. Nelsen, S. F.; Trieber, D. A.; Ismagilov, R. F.; Teki, Y. J. Am. Chem. Soc. 2001, 123, 5684-5694
55. Nelsen, S. F.; Tran, H. Q. J. Phys. Chem. A 1999, 103, 8139-8144
56. 6) in toluene at ambient conditions resulted in the rapid formation of a precipitate. Such species generally need to be formed in coordinating/polar solvents to remain soluble. See: Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910
57. Bender, T. P.; Graham, J. F.; Duff, J. M. Chem. Mater. 2001, 13, 4105